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Season Four

In The Five, Damon and Shane first met, although they were never shown speaking to each other directly and alone.

In We All Go a Little Mad Sometimes, Damon and Shane meet again, only under different circumstances. Damon and Bonnie need to ask Shane about the Hunter's Mark to help Elena, who is having horrifying hallucinations because of her killing Connor. Later in the episode, Damon finds out from Matt that the pastor made a call a day the last month he was alive to the same number, and 10 calls to that number on the day of the explosion—Shane's office.

In My Brother's Keeper, at the Miss Mystic Falls Pageant where Shane is a judge, Damon asks Shane why is he here. Damon then accuses Shane of convincing Pastor Young to kill the Town Council.

Outside, Elena and Shane are talking and Damon interrupts, threatening to kill Shane again. However, Shane later reveals that he could lead them to the Cure for vampirism, which Damon and Stefan and the others have been trying to find so they could give to Elena, and he knows this because he has already been there. Shane tells him and Elena that to find the Cure, they have to dig up the ancient immortal Silas, who is buried with it. Jeremy's Hunter's Mark so happens to contain the spell to free Silas, but Shane won't tell them where the location is, as it is his way of staying alive.

Damon tells Elena his theory about Shane having killed Pastor Young and the Town Council at the explosion at his farm, with Shane telling him that the pastor had lost his wife to cancer and he had sought him out for supernatural assistance. But he remarks that the pastor was "too far gone."

In Into the Wild, Shane leads an expedition (that to say, Elena, Damon, Stefan, Rebekah, Jeremy and Bonnie) to the island where Silas - and the Cure - are located. Shane offered Damon sunscreen, to which he replied, "Is that supposed to be a joke?" Later, when Shane was talking to Bonnie in his tent, Damon pressed for answers, and soon it becomes an interrogation, with Damon demanding to know where the Cure is. Shane tells him that the Cure and Silas are entombed in the caves. Turns out, Shane's dead wife, Caitlin, had convinced him to begin his quest for Silas so that she and their son could come back and that he needed three massacres to do so. Damon counts two massacres: the explosion at the Young Farm and the Sacrifice of the Twelve Hybrids, inquiring Shane on what the third one is. Shane begins to tell Damon to leave the island instead of watching Elena become human again and choose Stefan. This provoked Damon to try and kill Shane, but Elena luckily stopped Damon before so.

Damon: "Hey, no pity votes for April Young, okay? I mean, just because her dad blew up a house with a dozen people in it doesn’t mean she should get a tiara. But you knew him, didn’t you? Because I hear you two racked up a pretty impressive phone bill."

Shane: "Oh, you again. I must be the least intimidating mass murderer ever."

Damon: "Well, you still never gave me a name. And it’s kind of urgent."

Shane: "Listen, there is no other name. Look, at any given moment there are five Hunters in existence, alright. Most of them have no idea who they are or what their purpose is. It means finding more than one in a lifetime is next to impossible." (Shane walks past Damon and starts to leave the room. Damon uses his superspeed and rushes in front of Shane. Shane looks at him and laughs.) "Subtle."

Shane: "You know, since it’s generally unwise for a vampire to seek out a Hunter, it means you’re interested in the mark. It’s probably because of where it leads, but here’s the thing, even if you complete the mark and you get the map, the thing that you’re looking for is sealed with a spell only a certain kind of witch can perform."